My itunes match will not sync properly

Question

Mac User same thing
Hello there here is my problem. My itunes match will not sync properly. It shows a lot of songs over 100 with the icloud match status as "Waiting"
Here is what i have done
1. Reinstall the entire OS delete everything and start from scratch
2. Turn on and off itunes match.
3. Hold down the option key
4. Move my music out of the music folder clear everything out of my itunes and bing back my music.
5. Use backup copies of my music in case the music files had been corrupted.
6. Checked numerious mac community forms that report simular issues.
7. Tried another macbook pro that I have
8. My wifes account which has about 8000 songs did no have the issue. My account seems to have the issue sobeservices2. I beleive this to be account specific. My account has 11481 songs and about 100 to 100 show with the status of "waiting"
9. I get no error messages
10. I've tried multiple ISP - COMCAST - FIOS - I even tried multiple computers
11. Redid the entire os
12. My account has problems "*****s2" but my wife account does not
13. Replicated the issue on more then one computer it seems only has problems with my itunes account. Suck waiting to upload
and its not always the same songs sometimes it's different songs that it gets suck waiting to upload.
14. Removed the waiting songs and attempted again
15. Started with fresh iTunes had the server match a blank itunes folder  to the point where it said "0 Songs Match" then re-added them
16. Called Apple Care and spoke with a Senior Advisor who told me he would have to escalate a ticket and he to thought I had done all the tsing possible and that it was up to the engineers to figure out a solution.
I have been working on this for about 4 weeks now. All my trouble shooting has pointed it to be an account specific issue.
Any advise from the community

Answer 1

Hi
I have had a similar set of issues.  8000 songs, 800 in waiting.  All ripped from CD into Apple Lossless - mainly classical so most didn't match directly.
First I ripped all these 8000 songs for my father first on his laptop from his CD collection.  Eventually got them all matched or uploaded to his Match account (except one) by the usual tricks people suggest (e.g. recoding as AIFF or MP3 etc, deleting, re-adding blah blah). Though of course I shouldn't really have to waste my time doing this.  One song absolutely refused to upload. Tried everything - including buying a pristine downloadable version off the publisher's website.  Still resolutely refuses to upload.
Anyway - main problem is now with my PC. I copied all these 8000 tracks over. Re-installed everything etc.  800 remain in "waiting" (even though they uploaded Ok on a different account).  When I rip my own CDs even some common stuff (e.g. Bowie/Stones) gets uploaded instead or matched and often with one or two tracks stuck in 'waiting'.
If I then look at my IPad (with Match enabled), it will show these waiting tracks as if they were already downloaded to it (which of course they are not). If I try and play one of them it just skips over it.